Backstory: It’s hard to imagine the songs of anyone other than Simon & Garfunkel guiding the young, disillusioned protagonist the 1968 classic The Graduate as he returns to his parents’ opulent suburban kingdom, answers the obligatory stream of post-grad “What are you going to do with your life?” inquiries, and of course, navigates the ever-complex Robinson clan.

The soundtrack features several of the duo’s previously released songs. The Sound of Silence kicks the film off as Benjamin Braddock takes a forlorn ride on a moving walkway at LAX upon his return home from college. Later, as he oscillates between days by the pool and nights in bed with Mrs. Robinson, that track returns, and April Come She Will takes over, too, as a languid Dustin Hoffman spends his summer horizontally. Scarborough Fair/Canticle also soundtracks Braddock’s aimlessness and increasing melancholy as he deals with the consequences of trying to date the daughter of the mother with whom he’s been sleeping and later makes the trek to Berkeley to try and betroth the former. (“But what if she doesn’t want to marry you?” his mother asks. He’ll figure that one out when he gets there.)

Interestingly, the song most associated with the film, Mrs. Robinson, never actually made it into the movie itself, nor onto the accompanying soundtrack album. The film premiered at a red carpet event Christmas week in 1967 and Simon & Garfunkel recorded the full hit version of Mrs. Robinson weeks later in early February. The soundtrack LP was in stores in January. Forever linked in music and movie fans memories with the landmark motion picture, the song would go on to hit No. 1 during the summer of ’68 and then win two Grammys, including the much coveted Record Of The Year award, never before awarded to a rock-based artist.

Here’s to you, Mrs. Roosevelt: Director Mike Nichols was such a fan of the band that he reached out to Columbia Records chairman Clive Davis to license their songs for the film, eventually convincing Paul Simon to write an original or two specifically for The Graduate. Extensive touring delayed this deal, and Nichols proved to be unimpressed when presented with both Punky’s Dilemma and Overs (fear not; each would find a home on Bookends). But when he got a little taste of an unfinished number featuring the lyrics “Here’s to you Mrs. Roosevelt,” he simply said, “It’s not Mrs. Roosevelt, it’s Mrs. Robinson,” and the rest was history.

Where have you gone, Joe DiMaggio? Perhaps the most famous line, these lyrics came seemingly out of nowhere. As Simon once told SongTalk magazine, “The Joe DiMaggio line was written right away in the beginning. And I don’t know why or where it came from. It seems so strange, like it didn’t belong in that song, and then, I don’t know, it was so interesting that we just kept it.” Mickey Mantle might have been a more obvious name drop for Simon, whose Yankee fandom truly manifested during Mantle’s years. When the baseball star asked why DiMaggio was the chosen one during a commercial break on The Dick Cavett show, legend has it Simon replied with, “It’s about syllables, Mick. It’s about how many beats there are.”

The light drama continued when later, Simon met DiMaggio himself — who was displeased with the lyric with rumors of legal action brewing — at an Italian restaurant in New York. The musician says DiMaggio inquired as to “why you ask where I’ve gone. I just did a Mr. Coffee commercial, I’m a spokesperson for Bowery Savings Bank, and I haven’t gone anywhere.” The two patched things up, and Simon would go on to honor the baseball star upon his passing with an OpEd in the New York Times.